Guanidinosulfonylphenyl azo pigments having acetoacetamidophenyl coupling component radicals

ABSTRACT

ARE USEFUL FOR THE COLORATION OF PLASTICS, TEXTILES, PAPER, NATURAL RESINS AND RUBBER. THE RESULTANT DYEINGS ARE VERY FAST TO MIGRATION AND LIGHT AND SHOW GOOD HEAT STABILITY.   NH2-C(=NH)-NH2-SO2-C6H4-N=N-CH(-CO-CH3)-CO-NH-C6H5   PIGMENTS OF THE MONOAZO SERIES WHICH CONTAIN A NUCLEARLY BOUND SULFONIC ACID IMIDO-UREIDE GROUP AND ARE, E.G., OF THE FORMULA

United States Patent US. Cl. 260-193 3 Claims ABSTRACT OF THE DISCLOSURE Pigments of the monoazo series which contain a nuclearly bound sulfonic acid imido-ureide group and are, e.g., of the formula are useful for the coloration of plastics, textiles, paper, natural resins and rubber. The resultant dyeings are very fast to migration and light and show good heat stability.

This application is a continuation-in-part of copending application Ser. No. 691,707, filed Dec. 19, 1967 and now US. Pat. 3,598,803.

It was found that azo compounds of the formula C O-CH:

SO -NH-C-NH,

wherein each of nuclei A and B is either further unsubstituted or further substituted, suitable substituents for such further substituted nuclei including chloro, bromo, methyl and methoxy; are very useful pigment dyestuffs.

The new compounds are produced by diazotizing a guanidinosulfonyl-substituted aniline of the formula N H (II) and coupling the resulting diazonium compound with a compound of the formula 3,741,953 Patented June 26, 1973 The coupling reaction is conducted in the normal manner in a weakly acid, neutral or alkaline medium at room temperature or with cooling.

The new compounds have outstanding properties as pigments. They are virtually insoluble in the commonly used solvents and have very good rheological properties. Applications for which they are suitable include the dyeing of paper stock, the mass coloration of plastics in solution or other forms, the coloration of natural and synthetic resins and rubber, and the printing of textiles and paper.

It is advantageous to prepare the pigments in paste form before application. For thus purpose they are submitted to mechanical treatment in ball or roller mills or other suitable equipment and if necessary in the presence of dispersing agents, such as the condensation products of naphthalenesulphon-ic acids and formaldehyde. The pigment pastes can be used for pigmentation in the paste form as obtained, or they can be dried and the resulting powders ground.

In the aforenamed materials the pigments are outstandingly resistant to migration and fast to light, and have very good fastness to washing, chlorine, hypochlorite and peroxide bleaching, cross dyeing, blind vats, hydrosulphite, dry cleaning, rubbing, overlacquering and solvents. They show good transparency and heat stability.

The parts and percentages given in the following example are by weight and the temperatures are in degrees centigrade.

EXAMPLE 1 6.85 parts of 1 amino 2,5 dimethoxybenzene-4-sulphonic acid imidoureide are dissolved in 100 parts of water and 16 parts of 30% hydrochloric acid and subsequently diazotized at 0-5 with 25 parts of 1 normal sodium nitrite solution. The diazonium solution is filtered and adjusted to pH 3.5 with aqueous sodium acetate solution. 0.4 part of the adduct of 20 moles of ethylene oxide on 1 mole of oleyl alcohol are added. In the next 30 minutes a solution of 7.1 parts of l-acetoacetylamino-2,5-dimethoxy-4-chlorobenzene in 100 parts of water and 6 parts of 30% sodium hydroxide solution is allowed to flow in at 0-10 with stirring. Stirring is continued for 1 hour, then the reaction mixture is raised to 80-85 and filtered.

The filtercake is washed with water and vacuum dried at A yellow pigment in a yield of 14 parts is obtained; it is applicable, for example, in plasticized polyvinyl chloride (PVC), which it pigments in yellow shades, showing very good light fastness, heat stability and resistance to migration.

The tabulated examples which follow, give the formulae of further diazo components and coupling compo- (In) nents, which may be reacted as detailed in Example 1.

Exam.- ple Shade No Diem-component Coupling-component in PVC 2 O CH; (i) CH3 Yellow.

-01 -NH2 CHaC O CHaC ONH- 6 Representative pigments of the foregoing examples are 2. A compound according to claim 1 having the foras follows: mula OH: OCH: l 0011,

| 00 0am OCHa l 6 00-0113 SWQNEM Q01 Q O l S 2- N=N-CHC ONH -c1 NH CH: CH: l C=NH OOH; OOHa *Hg NH--CNH1 Example 1 L and 1 H 01 f OCH; 3. A compound according to claim 1 having the for- 0 mula N=N-dH-0 O-NHC1 01 Oz-NH-E-NH: 50H; 0043B: (IXJHa H Example 5 OI Having thus disclosed the invention what we claim is: CH3 1. A compound of the formula I H (JO-OH: References Cited UNITED STATES PATENTS 2,920,070 1/1960 Jirou et a1. 260-193 X FOREIGN PATENTS or a substituted derivative thereof, 1 392 484 2/1965 France 260 193 wherein each substituent is independently chloro, bromo, methyl LEWIS GOTTS. Primary Examiner or methoxy and C. F. WARREN, Assistant Examiner each substituent is attached to a phenyl ring.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No.. 3,741,953 Dated Ju ne 26, 1973 Inv n )Arm d Henrard Fritz Kehrer and Hans Wasem It is certified that error appears in the above-identified patent and that said Letters Patentare' hereby corrected as shown below:

Column 2 line 131- the word "thus" should be -this-.

Column 2 line 59 example 2 a OCH 1 7 should be OCH Column 5 line 5 example 1 3 E 3 s "N=NC "should read =N-CH-CO-NH- Signed and sealed this 24th day of September 1974.

(SEAL) Attest:

c. MARSHLL DANN McCOY M. GIBSON JR.

Commissioner of Patents Attesting Officer USCOMM-DC cow's- 69 I U.$. GOVERNMENT PRINTING OFFICE I!!! 0-366-384,

FORM PO-1050 (IO-69) 

